Servers not downloading all of the assigned updates

I have a mix of Windows 2008R2 and Windows 2003 servers at one of my clients. I approved Windows updates for the servers a couple of weeks ago. Most of the updates downloaded and installed with no problems, but I noticed at the time that some of the updates on several servers didn't download. These servers are set by group policy to detect and download updates but not to install them automatically. In WSUS, the computer "updates needed" report shows the updates under the Approval column as "Install" but the status column shows "Not Installed," where it should be "Downloaded."

Nothing has changed since the servers were restarted a couple of weeks ago after the initial installation of the other approved updates. I looked in the Windows Update log for one of the servers, but I can't find anything that stands out. It looks to me as though the server finds the update it needs (there's only one outstanding on this particular server) but just never downloads it.

There could be several reasons for this happening. One thing I have noticed is that some updates only apply if a specific service pack has been applied. We had a few 2008 servers that did not have SP1 on them. They were not receiving any new updates for several months. Once I installed SP1 on the server, suddenly it was downloading and installing needed updates from the past months.

The other problem could be an issue with the software distribution folder on the server. You can force the system to rebuild a new one.

@mpfister & arnold: The updates that are not downloading are:Windows 2008: Yes, the one mentioned by arnold is the update that is not downloading. It's 2698365, and according to the Windows Update log it is "{E06056E3-0199-4C68-8AC3-BDDDFF356A0A}.105" which I assume means it's rev 105.

Windows 2003: There are 4 updates that aren't downloading, all Windows security updates for Windows 2003: 2698365 (x64 and x32); 2509553, 2536276, and 2638806 (x64 only). I just now noticed, looking back at my WSUS console, that these are very old updates, but they must have just showed up in the downloads over the last month (I do Windows updates on these servers once a month). They're NOT showing as having been superseded in the console. And they are on the list of needed updates for these servers. Very strange!!!

Check the status of the update in WSUS console.Point the server to MS, for check updates to see whether this update is still reflected as needed.

one option you could download the update from MS at http://www.microsoft.com/en-us/download/details.aspx?id=30236

As was pointed out, the update could have been installed before, but something change triggering its "reflection" as needed but on a download attempt, something else is interferring. Check wsus to see whether the files/content is there.